Two Hearts Are Stolen
by MWolfL
Summary: A thief from Manehattan has arrived in Ponyville, but when Applejack meets him she finds that there's more to his story than she knew. She and her friends decide to help him out, and in doing so something happens to Applejack that she never would've predicted. ApplejackXOC
1. Thievery in Manehattan

A.N. I based Richie Fillyanthropy on Richie Rich from the 1994 film of the same name, and named other OCs after characters from said film.

It started out to be a nice sunny day, the usual day where nothing goes wrong. But that changed when Rarity saw something in the Ponyville Gazette.

"Oh dear...I'd better show this to Applejack." She said.

She quickly but daintily finished breakfast, and then trotted for Sweet Apple Acres with the newspaper. As she neared Applejack bucking apples she saw Big Mac and Apple Bloom nearby helping with the harvest.

"Well howdy Rarity, don't normally see you this time of-" Applejack saw Rarity's concerned look. "Is somethin' wrong?"

"It is, there was a thief in Manehattan." Rarity said. "And...well, you'd better read this. Start from here."

Rarity rested the newspaper on Applejack's pile of apples so that Applejack could read the article easily, and then Rarity tapped to a certain paragraph.

"The thief Richie Fillyanthropy was instantly banished from Manehattan due to his uncle, Lawrence Fillyanthropy, not wanting his nephew nearby anymore. This view was shared by Richie's victims, save for two who refused to comment-" Applejack's eyes widened. "Aunt and Uncle Orange!" She gasped.

"What?" Big Mac and Apple Bloom gasped.

"Oh no, Aunt and Uncle Orange have been robbed? They never wrote to us..." Applejack said worriedly.

"Well that's why I thought you should know, in case you wanted to go see if they're all right." Rarity said.

"Thank you Rarity, but unless they were among the more recent victims I'm sure we would've gotten word if they had been hurt." Applejack said. "One thing's for sure though, if this Richie varmint ever shows his face in these parts I'll teach him a lesson for robbin' from family."

"Eeyup." Big Mac frowned in agreement. "We'd better inform the rest of Ponyville in case he comes here."

Applejack and Rarity agreed, so Rarity went around to make sure that the rest of Ponyville had heard of the thief. By the afternoon, everypony had.

A few days later, late that night, the exhausted form of a unicorn stallion collapsed beneath one of the apple trees...

"Hey you!"

Groaning with exhaustion, the unicorn stallion - brown with a dark brown mane and tail and blue eyes - slowly opened his eyes to see an angry Applejack, Big Mac, and Apple Bloom in front of him.

"I recognize you from the newspaper, yer Richie Fillyanthropy!" Applejack glared.

"Thieves ain't welcome in these parts, so-" Big Mac raised a hoof threateningly.

"Okay okay, easy." Richie said calmly, much to their surprise. "I'm not going to hurt anypony, and I'm not here to steal anything. I was just exhausted and needed to sleep, but if you don't want me here then I'll go."

Stunned, Applejack, Big Mac, and Apple Bloom watched Richie sadly walk away.

"Hold on, why did you become a thief anyway?" Apple Bloom asked. "I mean your Cutie Mark doesn't even relate to stealin'."

Surprised, Applejack and Big Mac looked at Richie's flank and saw that Apple Bloom was right. Richie's Cutie Mark was the silhouette of a simple house inside a heart.

"Gee...Apple Bloom has a point." Applejack had to admit.

Richie turned back around with tears in his eyes.

"I'm not the thief, I was framed." He sobbed. "You see I come from a rich family, but when I was a little colt my parents went sailing and died in a storm. My Uncle Lawrence moved in and took over the family business, but only cared about making profits and didn't even care about me. When the neighborhood orphanage was in danger of being shut down last year I decided to 'steal' some of my parents' emergency money to save it. My uncle banished me from the house after that and spread rumors of me being a thief, later hiring somepony to do some actual thieving to make the rumors more believable. I had to go into hiding, but a few weeks ago I decided to sneak into my parents' home to look for their will, hoping that their business was left to me instead of my uncle. Unfortunately my uncle saw this coming and I got caught. You know the rest from the news."

Big Mac was wary at first, but softened upon Applejack looking at Richie as if she felt sorry for him.

"I believe ya." Applejack said softly. "Few ponies know more about honesty than I do, and I can tell when somepony is being honest."

Richie smiled with relief, but his eyes still looked sad.

"Sorry about bein' harsh towards ya earlier, but two of the ponies robbed were our Aunt and Uncle Orange and we happen to be very protective of our kinfolk."

"It's okay- The Oranges? They were old friends of my parents." Richie said with surprise.

"Really?" Apple Bloom said.

"Yeah, they were business associates. My parents invested in good businesses and community services for a living, mostly focusing on using their money to improve things for ponies everywhere." Richie explained. "The Oranges' business was one of the ones they invested in."

"Well I'll be..." Applejack was surprised by the fact that her family and Richie's family knew each other.

"Low blow for your uncle to frame you of robbin' old family friends." Apple Bloom frowned.

"Yeah...I hope they don't believe I was the thief." Richie sighed.

"Dunno for sure...accordin' to the article about your banishment they refused to say anythin' about the matter." Applejack said. "That could be for any reason. But tell you what, how about we write to them to explain what really happened?"

"Would you? I'd appreciate that, I don't want to end up on bad terms with them." Richie smiled, looking less sad.

"Of course. In fact..." Applejack smiled as if she was getting an idea. "I believe an old friend of mine can help you get your name cleared and reveal the truth about your uncle."

"I'd really love that, I want to take over the business and start helping others like my parents did." Richie smiled before looking confused. "But how can your friend help?"

"Well...she happens to be a princess." Applejack smirked. "The Princess of Friendship to be exact."

Richie dropped his mouth open.

In fact he was so stunned by the reveal that he didn't realize that he had been dragged to the Castle of Friendship until Applejack knocked on the door. Richie widened his eyes upon seeing the castle.

"Hello Applejack- Richie Fillyanthropy?" Twilight frowned with confusion. "Applejack, what's going on?"

"It turns out we've been wrong about Richie here." Applejack explained.

"Hm...you'd better come in." Twilight noticed that the ponies behind Richie and Applejack were whispering with disapproval.

Richie was overwhelmed by the throne room.

"Incredible..." He murmured. "I could never imagine a room like this. Well, except maybe in a fairytale."

"Really? Didn't you come from a rich family?" Applejack remarked with confusion.

"Yeah but my parents were always the humble type. Barely decorated our house." Richie shrugged. "In fact most of the expensive articles they owned were either heirlooms or artwork they enjoyed looking at."

"Oh."

Applejack then explained the truth to Twilight. Twilight dropped her mouth open near the end of it.

"That's horrible!" A male voice said.

It was of course Spike, who had just entered the room. Richie jumped a little.

"Sorry, never saw a dragon before." He explained.

"It's cool." Spike smiled before frowning. "I can't believe anypony would do that to a relative! Okay Blueblood I can see stooping that low, but still..."

"Prince Blueblood? Really?" Richie said with surprise.

"Oh yeah, just talk to our friend Rarity if you want a good story about his true colors." Spike sniggered.

"Oh. Glad my parents weren't into socializing with the elite then." Richie remarked. "Mostly they did for business reasons."

"Speaking of the elite, I'd better write to Princess Celestia about the matter." Twilight said. "A letter from her will exonerate Richie pronto."

"What about a letter from you Princess Twilight?" Richie said with confusion.

"Oh I don't have the power to do things like that, except maybe in Ponyville." Twilight shrugged. "And you can drop the princess, I may have earned the title but that doesn't mean I like being called princess."

"Oh, no problem." Richie smiled. "Always happy to meet a fellow member of the humble elite."

"In that case allow me to introduce myself: Prince Spike, Princess Celestia's adopted son and a humble dragon who just recently allowed his true status to be revealed so that he can start participating in court and helping his subjects." Spike smiled.

"Oh yes, I heard of you." Richie smiled. "You're also Twilight's assistant right?"

"Right, and metaphorical little brother." Twilight nodded, looking up from her quill for a sec before going back to writing. "There, that should do it."

"Okay, sending it now." Spike said before sealing the letter and sending it through his fire.

"Cool trick." Richie smiled.

"Thanks, mom taught me that one."

"Well, after we get Princess Celestia's letter I say we head to Manehattan to confront Richie's uncle." Twilight said. "Probably should limit the group though, a smaller group would be easier to sneak onto the estate."

"Oh that's no problem, I have my own special entrance that not even my uncle knows about." Richie smiled.

"Really? Good...okay, Pinkie Pie's in because of her Pinkie Sense, Rarity I know will want to come because she loves Manehattan, you're in of course Applejack because your aunt and uncle were two of the ponies robbed...and we might need Rainbow Dash's speed. Fluttershy I think won't mind missing out on the trip since she doesn't like confrontations."

"That's a good idea, my uncle can get really brutal when he's angry." Richie agreed.

"We'll definitely need Rainbow Dash then." Twilight deadpanned. "Starlight is still in the Crystal Empire so she'll have to be left out too, the sooner we do this the better."

Spike then burped out a message from Princess Celestia. Two actually, at the same time. One was unsealed so Spike unrolled that one first.

"Ah good, perfect timing." Twilight smiled.

"Let's see...Dear Twilight, I am shocked by the reveal of what Mr. Lawrence Fillyanthropy has done but I also have to admit I am not surprised. He happens to be an...acquaintance of my nephew Prince Blueblood, they went to the same school together." Spike read. "Well that explains a lot." He remarked sarcastically.

A.N. Celestia stopped using Twilight's title most of the time due to Twilight requesting it. She now only called Twilight by her title during formal occasions.

"Oh yeah, thought I heard of Prince Blueblood before." Richie noted. "My uncle must've name-dropped him one Hearth's Warming Eve or something."

"Uh where was...oh yeah: I have included a letter of pardon for Mr. Richie Fillyanthropy to give to the police so that he can be let back into Manehattan and take over his family's business. Sincerely, Princess Celestia." Spike finished reading.

"Good, we'd better get ready to go then. Oh Spike, do you mind missing out on the trip? I'd like you to take over here while we're gone."

"No problem, it'd take some self-control to keep me from toasting this Lawrence's flank anyway." Spike winked jokingly.

Twilight just smirked back.

After revealing the truth behind the thefts to the rest of Ponyville Richie received a friendlier greeting from everypony. Especially Pinkie unsurprisingly.

"Don't worry Richie, we'll give your uncle meanie what he deserves. I Pinkie Promise." Pinkie grinned.

"Pinkie Promise?" Richie repeated.

"Cross my heart and hope to fly, stick a cupcake in my eye." Pinkie recited.

"Oh."

"Speaking of cupcakes, would you like one?"

"Actually I would love one, I haven't had a decent meal in days." Richie admitted.

"In that case be right back!" Pinkie zipped into Sugarcube Corner and then zipped back with a few cupcakes and a milkshake.

"Thank you very much...say, did you ever consider participating in a professional racing event?" Richie remarked, a little taken-aback by her speed.

"Not really. Don't need to anyway, I do plenty of running here and partying is my main thing." Pinkie grinned.

Richie then ate, taking care not to eat or drink too fast.

"You say what's on yer mind dontcha?" Applejack noted.

"My parents taught me to always be honest, yet also take care to phrase my words so they don't hurt anypony." Richie smiled.

"Well, gotta say I respect that. Honesty is my main trait. Obviously Pinkie's main trait is Laughter." Applejack then chuckled.

"Not surprised." Richie grinned after swallowing a bite. "I'm guessing Friendship is Twilight's main trait."

"Yes, also Magic." Twilight nodded. "In my case the two kinda go together."

"Because Friendship is Magic?" Richie smiled.

"Why...yes. How did you know?"

"I always cherished friendship myself, always wanted it actually." Richie then looked sad again. "Didn't really get much of it as a colt, most of the other foals were just into the fact that I had wealthy parents. The orphans from the orphanage were really my only friends, but even then I couldn't hang out with them often since we went to different schools and they rarely left the orphanage."

"Oh..." Twilight said softly, understanding how lonely Richie must've felt.


	2. Confronting Lawrence

After Richie was done eating they headed for the train station and made the journey to Manehattan. Once they were there a nearby cop almost made a move to arrest Richie, until Twilight - who was actually wearing her crown - cut him off.

"Why- Princess Twilight Sparkle!" The cop gasped. "But...begging your pardon princess but what are you doing with a thief?"

"He's not a thief, and my friends and I are here to see that he gets justice." Twilight said firmly.

A.N. I figured that Twilight was never recognized as a princess in Manehattan before because she wasn't wearing her crown. I wouldn't be surprised if most Manehattanites believed that Princess Twilight would never make a public appearance without her crown. Especially since Celestia never does.

"Richie!"

Startled, everypony turned and saw Mr and Mrs. Orange head over to Twilight and her friends.

"What are you doing back darling, you know the police will put you in jail." Mrs. Orange said concernedly.

"I know, I only came back because some new friends of mine - including your niece - are here to prove my innocence." Richie smiled, glad to find out that the Oranges still cared about him.

"Oh good, we never did believe that you were the thief." Mr. Orange said haughtily. "The nerve of those reporters claiming that you were, that was why we didn't even want to see them."

"It wasn't their fault, Richie told us that his uncle framed him." Applejack said.

"What?" Mr and Mrs. Orange gasped.

"Oh I should have known, that pompous bit-pincher." Mrs. Orange frowned. "Obviously he wanted all of his brother's money for himself. Oh if there's anything we can do for you Richie darling, just name it."

"Actually, can you do us a favor and deliver this pardon from Princess Celestia to the nearest police headquarters for us?" Twilight asked. "We want to confront Richie's uncle as soon as possible."

"Of course Twilight." Uncle Orange smiled.

Surprised, Twilight turned to Applejack questioningly.

"Wrote them a letter sayin' that you prefer to be addressed without the princess title a while back." Applejack chuckled.

"Oh. Thank you Applejack." Twilight smiled. "Well everypony, we'd better get going."

"Indeed." Mrs. Orange agreed. "We hope to see you all soon after this matter is cleared up."

"I hope that too." Richie smiled.

All of them then left, the Oranges for police headquarters with the pardon and Twilight and her friends for Richie's old home.

Of course they had to take a few taxis there, because Richie and his parents had been so wealthy that they could afford a three-story house in Manehattan instead of one of those wealthy condos (let that sink in for a moment). Meaning of course that Richie's house was far away from the downtown shopping district.

However Richie had the taxi stop behind the house, which was possible because there was a street between it and the front yard of the next house due to the backyard being that huge.

"Don't want my uncle to see us coming, fortunately he wasn't as fond of nature as my parents were." Richie explained to the others.

He used his magic to create a path through the hedge, and the group sneakily followed Richie to one side of the house.

"Here's my secret entrance." Richie smiled before pushing back a bush a little and using his horn to open a hidden door in the wall.

"Way awesome." Rainbow Dash whispered with a smile.

"Thanks, I enjoyed playing pretend when I was a colt and one of my favorites was pretending to be a secret agent." Richie whispered with a smile back.

They then quietly started to walk through the secret passageways.

"Uh-oh...guys, my Pinkie Sense just told me that somepony is being hurt over there." Pinkie suddenly whispered, pointing down one passageway.

"But that way is the kitchen-" Richie's eyes widened and he hurried in the direction Pinkie pointed in.

The others followed him, and saw him use his magic to open a door into darkness. Richie went in, and in a moment the dark was replaced with light. They instantly saw that Richie was by a light switch, and that they were in a pantry. They could hear sounds of whipping.

"I have had enough of your stupid riddle!" A mean and gruff male voice said. "Tell me where the Family Vault is now!"

Looking upset, Richie opened the pantry door. Everypony else could see that the next room was a kitchen...and also saw a mean-looking dark brown unicorn cracking his whip at two Earth pony servants!

"No, because you don't deserve to find it!" The male servant, most-likely the butler, glared; he was tan with gray hair, similar to Mayor Mare except it most-likely was real instead of dyed.

"Why you insolent-!" The dark brown unicorn - no doubt Richie's Uncle Lawrence - prepared to actually strike the butler with his whip!

"No!" Richie suddenly cried, leaping in-between the two.

This caused Lawrence to strike Richie with the whip instead! Lawrence gaped as Twilight and her friends gasped.

"Richie!" The butler and the female servant - probably a cook - rushed over to him; the cook was light blue with white hair.

"Wha- How did you get here?" Lawrence demanded before turning to where Richie came from...and widening his eyes upon seeing Twilight and her friends. "Oh...Princess Twilight...uh..."

Before he could utter another syllable, Twilight used her magic to tie Lawrence up with his own whip. She then zapped Lawrence's horn so that he couldn't use his magic.

"Disgusting." Twilight glared at him. "Whipping innocent ponies like that."

"Indeed, you make me ashamed to be a unicorn." Rarity agreed, also glaring at Lawrence.

Applejack, Rainbow Dash, and even Pinkie glared at Lawrence as well before they all went over to Richie. He had a nasty gash in his side, but otherwise was fine.

"Oh Richie dear, I'm so sorry this happened." The cook petted his mane affectionately.

"Don't be, I'm just glad he didn't hurt either of you instead." Richie smiled.

"Even though it isn't good that you got hurt, it is good seeing you again." The butler smiled.

"Same...I missed you both."

"Um, sorry to interrupt but I think it'd be best to continue this where Richie will be more comfortable." Twilight said. "Don't worry about Lawrence, I took care of him."

The butler and cook nodded and let Twilight use her magic to levitate Richie to the living room where he could rest on a couch. Even though her study of medicine was somewhat limited Twilight was able to heal Richie enough to at least stop his bleeding. Rarity then donated a long ribbon from her suitcase to use as a temporary bandage.

"Everypony, this is Herbert Martingale and Diane Bridle. They were the butler and cook for my parents, and second parents for me." Richie introduced. "After my parents died they were the ones who took care of me."

Twilight, Applejack, Rarity, Pinkie Pie, and Rainbow Dash introduced themselves. Richie then quickly explained why he was back and why they came with him.

"So, what riddle was that meanie talking about?" Pinkie asked.

"It was a riddle Richard and Regina told us to tell Lawrence if he ever asked about the Family Vault. They didn't want Lawrence to find the vault until he could properly answer it." Herbert explained.

"Family Vault?" Rainbow Dash said.

"Yeah, my parents kept their most precious treasures in it." Richie explained.

"So what's the riddle?" Twilight asked.

"The vault is hidden behind the most valuable thing in the world." Diane said.

Confused, Twilight and her friends looked around trying to figure out what it could be. Applejack then noticed something: a large painting of Richard and Regina with a much younger Richie.

"Hey, I think I might have found it." She said, going over to the painting.

Herbert and Diane were stunned, while Richie opened his mouth slightly and then smiled.

"What do you mean?" Rainbow Dash asked.

"The most valuable thing in the world is family." Applejack smiled.

She pressed her hooves along the bottom of the frame, until she hit a button. The painting swung into a secret room.

"Heh, no wonder Lawrence couldn't figure it out." Twilight smirked.

"Way to go cuz!" Pinkie bounced.

"Aw, t'weren't nuttin'." Applejack rubbed the back of her head humbly.

Richie got up off the couch, and led the way into the room. He turned on a light, and paused for a second. Twilight and her friends looked in as well and were stunned but then touched. No gold, jewels, or even sacks of bits. Instead there were old toys, photo albums, books, baby things, and a few bowling trophies. They started going further into the room, and upon closer inspection Twilight and her friends saw that Richard and Regina had won the trophies together.

"Your parents loved bowling huh?" Rainbow Dash said.

"Yeah. More of a baseball pony myself." Richie smiled before looking sad. "Didn't get much of a chance to play a real game though, closest I got was my dad hiring professionals coaching me."

"I understand your loneliness, I didn't get to really hang out with friends myself. Didn't even have my first slumber party until after I moved to Ponyville." Twilight said sympathetically. "It was mostly my fault though, I was too into my studies back then."

"Well, at least we have real friends now- Goldie!" Richie suddenly beamed and picked up a Golden Retriever plushie before hugging it. "Man I've missed you."

"Hid him in here back when your uncle insisted that you grow up, along with the rest of your old toys and books." Diane smiled.

"I know, I remember Herbert telling me one day after I came home from school." Richie smiled.

"How come they didn't wait until after you came home before moving everything here?" Rainbow Dash asked.

"Lawrence was coming home from work early that day." Herbert explained.

"Oh."

"He's so cute." Pinkie giggled, patting Goldie on the head.

"Thanks, my parents got him for me one Hearth's Warming Eve." Richie smiled. "Always wanted a dog, but I was too young to have a real one for a pet at the time..."

Richie suddenly turned around, remembering that he had seen photo albums earlier. Emotional, he set Goldie down and went over to them. He opened the first one, filled with photos of his parents dating and getting married. Everypony else just sat or stood there silently, knowing that Richie was going through a lot of sadness and pain at the moment.

Then, Applejack slowly walked up to him. When she got closer she could see tears forming in his eyes. She sympathetically put a hoof on his shoulder.

"I know how you feel..." She said softly. "I lost my parents when I was a little filly...Apple Bloom was just a baby at the time."

Richie sniffled a bit.

"It isn't fair how good ponies sometimes die before-" Richie stopped because he had still been turning pages in the album, only to spot an envelope hidden amongst the pages. "Could it be...?" He actually started to smile a little, using his magic to lift up the envelope and take a sheet of paper out of it. "It's my parents will!" He gasped happily.

"Really? What does it say?" Rarity smiled.

"It says that I inherit the house, the business, everything, with Herbert and Diane acting as my guardians until I'm old enough to run everything by myself." Richie grinned.

Everypony else cheered, until there was a loud knock at the door.

"I'll get it." Herbert left; a few moments later: "Oh, hello officers. Can I help you?"

"Yes, we got a letter from Princess Celestia pardoning a Mr. Richie Fillyanthropy for thievery due to having been framed by his uncle Mr. Lawrence Fillyanthropy." One officer said. "We've come to take him in for questioning."

"You can easily pick him up now, I got him tied up in the kitchen." Princess Twilight showed herself to the officers.

Her friends, Richie, and Diane soon followed.

"Oh, Princess Twilight Sparkle." Another officer said as he and the two other cops there bowed. "Didn't know you were here."

"Never mind that." Twilight waved a hoof dismissively.

"So you said you had him tied up? He must have done something horrible." The first officer said.

"Very horrible."

Twilight quickly explained as Richie went back into the vault to grab the will and close the photo album.

"Right, we'll take him downtown." The first officer said. "Mr. Fillyanthropy, you are under arrest for framing your nephew for thievery and assaulting two innocent ponies."

Since he was still tied up, the officers merely levitated him towards the paddy wagon. Richie showed himself.

"Mr. Richie, I am glad to hear that you are innocent of thievery." The first officer smiled. "It sounds like you'll be taking over your home and family business."

"I was supposed to anyway, I found my parents will in one of their old photo albums." Richie smiled, levitating the will towards the officer.

The officer took it with his own magic and glanced it over.

"Looks legit to me." He said before handing it back. "Doesn't matter either way at this point though. Oh, be sure to stay here for a while. You'll be called in to court to press charges against your uncle."

"No problem, there are some changes I'd like to make regarding how my uncle ran things anyway." Richie replied. "For one thing, I want to see how the orphanage is doing."

"The orphanage? They ran into financial trouble again so your uncle shut it down a couple moons ago."

"I was afraid of that." Richie frowned. "I'd better get that taken care of first, the sooner the orphans get a roof over their heads the better."

"I agree. Well, I'd better help my partners escort Mr. Fillyanthropy to headquarters." The first officer left. "I'll see you later."


	3. Beginning the New Orphanage

"Hm...Herbert, Diane, are there any abandoned buildings around here that could become the new orphanage?" Richie asked.

"We're afraid not." Herbert shook her head.

"Drat..." Richie then beamed. "I got it, I'll turn my home into the new orphanage."

Even Herbert and Diane looked stunned by the idea, but then Herbert and Diane smiled proudly.

"You'd really do that?" Applejack asked, never having met a unicorn that selfless before.

"That is exceptionally generous." Rarity smiled.

"Well, the little foals need a home and my home is too big for me anyway." Richie smiled. "Now, the bedrooms of course will still be bedrooms...I think I'll turn my parents' old bedroom into the caretakers' bedroom...the other bedrooms can be for the fillies, colts, and babies...good thing mom and dad wanted a place with plenty of guest rooms."

"What about you?" Twilight asked.

"Oh I'll just move into the attic, I don't need a fancy room anyway." Richie shrugged.

Twilight and her friends were even more surprised.

"Now I'm gonna need a list of poorly-off ponies, I'd like them to help with the painting." Richie brought out a sheet of parchment, quill, and ink out of a nearby desk and started writing things down. "That way they can get a little extra income for food and other necessities."

"Painting?" Rainbow Dash said with confusion.

"Yeah, the current paint job is too fancy for babies and foals. I'll talk to Gloria and Omar Horsepitality - they were the caretakers of the old orphanage - before changing the paint job in my parents' room though. I'd better go through all the fancy stuff here first too." Richie brought out another sheet of parchment. "I think I'll just move my parents' stuff from the vault into the attic with me, and I'll donate my uncles items to charities. He won't need them in jail anyway. As for my stuff I'll just keep the items I'm emotionally attached to and donate the rest to the orphans."

"Want us to help?" Applejack smiled.

"Sure thing, there's a lot to go through here. First let me separate my uncles' items with Herbert and Diane's help since we actually know which ones they are, then you can help with the rest." Richie smiled back.

Richie, Herbert, and Diane quickly went through Lawrence's stuff, which didn't take long because he only had knickknacks and some artwork. The rest of his stuff was back in his old home because he liked Richard and Regina's furniture enough to not replace it with his own.

Then Twilight and her friends helped Richie with the rest of the stuff. First they cleaned the attic, and then they moved his things from his old bedroom up there.

"Right...that'll do for today. It's getting close to dinnertime." Richie noticed the time on the clock.

"Well, fortunately for you all I have already made dinner." Diane smiled as she entered the room.

"Wonderful, I missed your cooking." Richie licked his lips before turning to Twilight and her friends. "Please join us, consider it my way of thanking you all for your help."

"Of course." Twilight smiled...before her stomach growled. "Heh, my stomach would hate me for turning you down anyway." She then blushed.

The others' stomachs were growling as well, so they only smiled in agreement.

After dinner Richie offered to let them stay in the guest bedrooms since there was still work to be done. They agreed due to it being more logical than going back downtown to book a hotel.

A couple days passed as they continued moving furniture around. Richie had his uncle's things sent to charity auctions, the attic got fixed up with his own things, and the fancy furniture the orphans would have no use for was also given to charity. Only Herbert and Diane's rooms were untouched since they will still be sleeping there ever after the orphans move in.

"Say, what about the Family Vault?" Pinkie Pie asked.

"I was thinking of turning that into the playroom, I just gotta move my parents' things out of there and figure out which items I want to keep." Richie said. "Twilight, can you help me list all the items?"

"Of course." Twilight grinned.

With Twilight's help they listed everything, and then separated the items into two lists: Richie's Things and Richard and Regina's Things. Then the others moved Richie and Regina's things into the attic while Twilight helped Richie decide which of his things would stay in the playroom and which of his things he'd keep. Goldie of course he was going to keep, and he decided to not donate his books to the orphans since they were first or special editions.

"First editions and special editions aren't exactly appropriate for foals who aren't into books." Richie explained. "So I'll just replace them with regular copies and keep the first and special editions for myself."

"Makes sense." Twilight nodded. "What about your other toys?"

"I'll have to go through each one individually. Then after I've made my decisions we'll take everything out. The items I'm going to keep will go into the attic, and the items for the playroom will be set aside until after the playroom is properly decorated and furnished."

After selections were made, the items for the playroom were boxed up to keep them safe and together until the playroom was completed. The items Richie was going to keep were put away in the attic properly.

"Good, that's everything except for the painting. Herbert, did you do the research I asked for?" Richie said.

"Sure did, I got a list of the poorest ponies in Manehattan. We can contact them soon and see if they're willing to do the painting for us." Herbert smiled before pulling a list out of his saddlebags.

Richie took the list with his magic and looked it over.

"Good...we'll have the ones who are good with painting do the detail work and the ones who haven't done much painting do the basics."


	4. Getting to Know Each Other More

"Um, beggin' yer pardon Richie but...what about the painting of you and your parents in front of the Family Vault?" Applejack asked.

"Oh I've been thinking about that. While a 'secret entrance' for the playroom would be cool I decided it'd be better if the playroom didn't have a door. I want it to be welcoming for all the foals after all, plus I'd kinda like to move the painting to the attic." Richie looked a little sad at that point.

"We understand." Fluttershy said sympathetically.

"Yeah. Hey, want me to help move the paintin'?" Applejack offered. "I mean we'll need Twilight's magic to properly detach it from the wall, but I'm more than willin' to help move it upstairs."

"Thank you, that'd be great." Richie smiled.

Applejack couldn't help but smile back. To be honest, she was growing fond of Richie. Not only did he have a love of family strong enough to compare to her love for her own family, but he was also willing to work hard to help others and at least as generous as Rarity if not more, a trait Applejack rarely saw in high-class ponies.

Richie had also grown fond of Applejack for her honesty, which was very refreshing after experiencing his uncle's dishonesty and treachery, and her strong love of family. And he really wanted to get to know her more, so after Applejack helped him move the painting to the attic he made a decision.

"Say Applejack, how would you like to go out to dinner tonight?" He asked.

"You mean all of us as a reward for our hard work?" Applejack guessed.

"No...I was actually thinking just the two of us...to thank you for your help. After all if I hadn't met you I wouldn't have been able to prove that it was my uncle doing the thieving."

"Oh..." Applejack couldn't help but blush a little since she had never been asked out before. "Um...I don't know..."

"I understand if you're too uncomfortable to go to any fancy restaurants, so we can go to a simple one." Richie offered. "I prefer filling simple meals to skimpy fancy meals myself anyway. Have ever since I was a colt."

"Well...okay then." Applejack smiled, now feeling better about the offer and not wanting to be rude. "I'm with you, better to fill yer stomach for a few bits than empty yer bank account over a meager meal."

"I know, I'll never understand why some ponies always go for the fancy stuff. I mean are they trying to lose weight they don't need to lose or something?" Richie grinned.

Applejack actually laughed at that, and Richie smiled. He liked the sound of her laugh. In fact he had grown to really like the sound of her voice in general.

After setting up the painting they went back downstairs.

"Oh, will I still need to get fancied up or anythin'?" Applejack asked.

"Nah, though you probably should brush your mane. I'm gonna brush mine as well." Richie said.

"Ah, good idea."

"Fancied up for what?" Rainbow Dash asked.

"Well, all of this is really thanks to Applejack, since it wouldn't have happened if I hadn't met her, so to thank her I asked her to have dinner with me tonight." Richie explained. "Plus I want to get to know her more, I have a feeling that we could become great friends."

"You know, I've been havin' that feelin' myself." Applejack smiled. "But only as long as you get to know the rest of my friends more as well."

"Of course, I want to get to know them better too." Richie smiled.

"Well, since Applejack will be busy with Richie how about the rest of us treat ourselves to a night out?" Rarity suggested to the rest of her friends before turning to Herbert and Diane. "You're welcome to come with us if you want."

"I'd love to, I haven't had a night out in years." Diane smiled.

"Me either, I could use the break." Herbert agreed.

"Okay, how about dinner and a spa treatment?" Twilight offered.

"Um, can we skip the spa?" Rainbow Dash winced.

"Oh yeah...sorry I forgot. How about seeing if a community play is going on instead?"

"I can contact Coco Pommel about that if you'd like." Rarity offered.

"Good idea."

"Coco Pommel?" Richie said with confusion. "Sorry, when I had to go on the run I ended up cut off from any new developments."

"Oh she's a friend I made during Fashion Week over two years ago." Rarity explained.

"Oh."

So everypony made their plans. Richie took Applejack to his favorite restaurant while the others went to a different restaurant and later went to a community play (Coco contacted them before they left confirming that one was going on). The play turned out to be The Wizard of Az, one of the plays Coco was in when she was a filly.

A.N. I went with Az as an abbreviation of aztouria, which is the cramping of horses' large muscles. Probably not fitting, but sometimes the names of pony versions of human things don't make sense anyway.

During dinner Richie made a confession:

"To be honest Applejack, I also wanted to spend some time with you alone because I have to tell you something." Richie said.

"Really? What?" Applejack tilted her head a little.

"Well, the truth is I've grown fond of you. You're honest, kind, and you have a deep love of family. Before I met you I thought I'd never find a mare with those qualities." Richie blushed a little. "However I understand that you're too down-to-Earth to date a Manehattanite from a wealthy family, after all a lot of wealthy Manehattanites can be snobby, but I still had to be honest about my feelings."

Applejack blushed, realizing that Richie had gotten a crush on her.

"Well, I at least have to express my gratitude for yer honesty." She said, looking down awkwardly a little. "The last time a unicorn got a crush on me he just tried to woo and impress me. Didn't even know why he was actin' that way until he said that he was plannin' to move to Ponyville and live on a farm. If he had told me how he felt from the beginnin' it would've saved us both a lot of awkwardness."

"Really? Gee, I know unicorns are usually too shallow to consider dating an Earth pony so who was it who got the crush on you?"

"Trenderhoof."

"Oh of course." Richie face-hoofed, chuckling. "I should've realized it before. I've read his articles and he often praises Earth ponies for their work ethic. Even once wrote that he has a soft spot for that work ethic."

"Yeah I know, he told me once." Applejack deadpanned. "However his so-called 'charms' didn't impress me one bit."

"Hoo boy, sounds like he went too far trying to win you over."

"You kiddin'? When he said he was movin' to Ponyville he was wearin' overalls and a straw hat." Applejack scoffed. "Can you believe it? Some ponies just can't seem to tell the difference between a farmer, a cowpony, and a hillpony. I happen to be both a farmer and a cowfilly, and I certainly ain't no hillfilly."

A.N. I know Applejack was amused by Rarity dressing up in overalls and a straw hat, but there was a difference between Rarity dressing up that way and Trenderhoof dressing up that way. Rarity mostly went to Canterlot whenever she traveled on her own, and so wasn't as educated about country life. Trenderhoof on the other 'hoof' traveled all over Equestria, and so should've known better than to dress in a stereotypical manner.

"Ay-yi-yi." Richie face-hoofed again. "Some ponies just don't do enough research. I mean once you learn more about them the differences are glaringly obvious."

"Exactly, thank you!" Applejack agreed with both relief and amusement.

They both laughed a bit at that.

"You know, I'm glad Trenderhoof didn't win you over. I really would like a chance to hang out with you more often." Richie admitted. "Plus I could tell from Trenderhoof's articles that he's full of himself and you deserve somepony more humble anyway."

"I agree to that...'hang out'? Not 'date'?" Applejack said questioningly.

"Yeah, because if you're not fond with actually dating then I'm fine with just hanging out." Richie explained.

"Ah." Applejack blushed. "Well yer right, I ain't ready to date yet. However you are humble, plus generous, hard-workin', and you have a strong love of family, so I wouldn't mind givin' ya a chance by hangin' out with you."

Richie let out a breath of relief.

After dinner they realized that they still had time to make it to the community play, and so decided to join the others. After the play was over they introduced Coco Pommel and Richie Fillyanthropy to each other.

"I'm really glad the Midsummer Theatre Revival is back, I missed seeing the plays." Richie said.

"Well it's thanks to Rarity and especially Applejack that it's back." Coco smiled. "Rarity did help me with the costumes, but Applejack was the one who helped restore the sense of community here."

"Really?" Richie turned to Applejack with surprise.

"Oh yes, she got the idea to make a simple stage in front of the street so that the ponies who were passing by at the time would stop and watch." Rarity smiled. "It worked too, after remembering how much they enjoyed the plays they realized that by working together they could completely restore the park and original stage."

"Wow. I have to say I'm impressed and grateful to you for that." Richie smiled to Applejack. "Charity Kindheart was one of my parents' best friends, and the Midsummer Theatre Revival was one of their favorite community projects."

"Oh I remember you and your parents now." Coco smiled. "You three almost always saw every play. I think you were even in a play once."

"Yes, Barley and the Chocolate Factory. I was Barley." Richie smiled.

"That's right! I played one of the Oompa-Loompas." Coco giggled.

"That explains why I didn't recognize you, those Oompa-Loompa costumes can really hide a pony's identity." Richie chuckled.

"I'll say. I am sorry to hear about your parents though." Coco then looked sympathetic.

"Thank you. Charity was too, in fact my parents' death was one of the reasons why she moved away." Richie remembered. "I remember how depressed she was during the funeral, and afterward she told me that she saw how heartbroken I was. She then told me that she realized that she didn't have that many years left, and so decided to be closer to her grandfillies so that they could spend more time with her before her time was up."

"I can't blame her." Applejack admitted.

"Me either. You know Applejack, I'm sure my parents are very proud of you for helping to bring back the Midsummer Theatre Revival." Richie then smiled.

"Aw shucks." Applejack blushed a little. "I'm just glad to help out. And I wish I could've met them."

"Me too, and I wish I could've met your parents as well." Richie agreed sympathetically.


	5. Romantic Advice

It was the day after tomorrow, and Twilight and her friends arrived at the Fillyantrhopy estate, soon to be the new orphanage. Since the painting had begun they had to move to a hotel, but they didn't mind needing to take the long journey. After all getting the orphanage ready was the most important thing right now.

"Glad to see you all, you can help me select furniture for the orphans." Richie smiled outside with some furniture catalogs near him.

"We'd be happy too...um, am I correct in assuming that Herbert and Diane are supervising the painting?" Rarity guessed.

"Yeah, they already know which basic colors I selected for each room and what pattern I want for the nursery." Richie nodded. "I'm going to let the foals decide what designs will go on their walls."

Suddenly, a carriage pulled up in front of the estate with a moving van behind it. The driver of the carriage got down and opened the door...for Mr. and Mrs. Orange.

"Aunt Orange, Uncle Orange, what're y'all doin' here?" Applejack smiled, going over to greet them.

"Seeing our niece again, plus we have a donation for the new orphanage." Mr. Orange smiled.

"Yes beds. Fine quality, without being too fancy for the little ones." Mrs. Orange smiled. "Richie darling, we are so glad that you've taken over the family business. However I am confused, I thought your uncle was going to be put on trial soon."

"He was, until the pony he hired to frame me confessed" Richie explained. "Just got the message from the police this morning, it turns out the pony my uncle hired was one of his servants and my uncle threatened to fire him unless he agreed to do some stealing and make it look as if I had done it. The servant only agreed because he really needed the job in order to take care of his family. However after my uncle was arrested the servant instantly entered the headquarters and told them the whole story. Turns out he had been feeling awful all these years for what he did, but was too afraid to admit the truth earlier."

"Which servant was it?" Mr. Orange asked.

"Don't know, the servant insisted on staying anonymous since he didn't want his family publicly shamed." Richie shrugged. "However I do know that the servant is in jail now, he got a lighter sentence for confessing but the fact is he still stole from others."

"It's too bad his family has to suffer." Twilight said. "If he had revealed his identity we could help his family."

"I know, I would like to help his family but for now there's nothing we can do." Richie sighed. "Anyway, thank you both for the donation but moving the beds inside will have to wait until the painting is done. Shouldn't be long though, a lot of ponies came to help."

"No problem, we can still unload the beds here. No sense in letting these hardworking stallions wait when I'm sure they have other jobs to do." Mrs. Orange smiled.

So except for Mr. and Mrs. Orange they all got to work unloading the beds and setting them down on the grass. The beds were fit for foals too, and there were even some cribs for the babies.

After that was done one of the painters came out.

"Oh Richie, the painting is all done if you'd like to take a look." She said.

"Sure thing, just a moment." Richie smiled before turning to Twilight and her friends. "Would you ladies mind picking up the orphans? The police told me that they were moved into a community center, and I contacted Gloria and Omar Horsepitality yesterday to let them know the good news. Here's the address." Richie used his magic to pick up a nearby piece of paper.

"Of course." Twilight smiled, taking the piece of paper.

"But how are we going to move all the orphans from there to here?" Pinkie asked, pointing with her hooves at 'here' and 'there' so that they crossed.

"I already set up a contract with a bus yesterday, just tell them I sent you and they'll send you there in a bus." Richie said. "Just be sure to give the address to the bus driver since I wasn't able to tell the company the address, the stallion I talked to was really busy and had to go to a meeting."

"Boy you work fast." Rainbow Dash remarked.

"Heh, inherited that from dad. He always was good at negotiating." Richie chuckled.

"Well, I admire that in a pony." Applejack smiled, before looking a little awkward.

Richie blushed at the compliment.

"Oh Applejack, do you mind staying here with us? We'd like to talk to you for a bit." Mrs. Orange said.

"Not if my friends don't mind." Applejack smiled.

"It's no problem at all, you go ahead and catch up a bit with your aunt and uncle." Rarity smiled. "Actually I was thinking of staying behind as well, to plan which beds should go into which room and also plan other bedroom pieces to get."

"Yeah, it doesn't take an army to transfer a group of ponies from one location to the other." Twilight chuckled.

"All right then. Oh, be careful around Pee Wee, he's a rambunctious little foal." Richie chuckled.

"Got it, see you guys later." Rainbow Dash waved as she, Twilight, and Pinkie left.

Rarity headed straight for the beds, taking the catalogs Richie was looking at earlier with her.

"You know dear, it's actually an interesting coincidence that you and Richie befriended each other now." Mrs. Orange said to Applejack.

"It is? Why?" Applejack said with confusion.

"Remember when you stayed with us wanting to become a Manehattanite? Well we had planned on introducing you to Richie around that time but you left before we could arrange it." Mr. Orange explained. "After all Richard and Regina were really good friends of ours and the four of us had hoped that you two would become good friends as well."

"Wait, you wanted to become a Manehattanite?" Richie raised an eyebrow towards Applejack.

"Yeah, back then I was blinded by the glamour of a sophisticated life and didn't know how lonely and borin' it was- Oh, no offense." Applejack then turned to her aunt and uncle.

"None taken, after all the sophisticated life isn't for everypony." Mrs. Orange smiled.

"We're just glad that you two are friends now, and we're sure that Richard and Regina are glad as well." Mr. Orange said.

"Huh...you know I remember that back when I was a colt my parents told me that they wanted me to meet a niece of Mr. and Mrs. Orange. That must've been you Applejack." Richie said. "Heh, back then I was at that age where colts weren't into befriending fillies, so I asked them why. They told me that I might actually like this filly because she was a tomcolt deep down. They were right, I'm glad you're a tomcolt instead of being feminine like most other mares."

"Well I'm glad yer humble and aren't shallow like most other high-class unicorns." Applejack chuckled back.

Richie blushed a little again.

"Oh my...are you two dating?" Mrs. Orange beamed.

"This is even better than we and Richard and Regina expected." Mr. Orange smiled.

"Oh, uh, not really." Richie said awkwardly. "I mean...I do really like Applejack...enough to want her to be my very special somepony even...but she isn't ready to date yet so we're just hanging out for now."

Applejack couldn't help but blush as well. She knew that Richie was fond of her and had become attracted to her, but it was now sounding as if he was actually in love with her.

"Oh..." Mr. Orange tried to hide his disappointment but wasn't very successful.

"Applejack dear, may I speak to you in private for a moment?" Mrs. Orange asked.

"Er...okay..." Applejack said reluctantly.

They went to where they would be somewhat out of earshot of Richie and Mr. Orange.

"You really like her?" Mr. Orange then smiled to Richie.

"Yeah, I never met a mare like her before. She's kind, honest, hard-working, loves helping others, and has a strong love of family." Richie sighed. "In fact...I think I'm even in love with her."

"You should tell her then."

"I will after she's ready to start dating, I don't want to unintentionally pressure her or anything."

"Dear, how come you aren't ready to date yet?" Mrs. Orange asked Applejack. "After all you are more than old enough."

"I know, but I'm a workin' mare from a farm. I don't have time for workin' the farm and a very special somepony." Applejack said.

"I understand your devotion to your family and the farm, but that is still a ridiculous statement. You can work the farm and have a very special somepony at the same time, you just need a very special somepony who understands your work ethic. And Richie is that type of stallion, in fact I'd go as far as to say that he's the best stallion for you. You really deserve a very special somepony, and it would be a shame for you miss out on the best chance you'll ever get just because you aren't sure you can balance things."

"Well..." Applejack hesitated.

"Um pardon me for intruding, but I couldn't help overhearing your conversation." Rarity came up to them. "You know Applejack, when I was unsure about ending up with Spike Cadance told me to listen to my heart. Maybe you should try that."

"Sound advice, thank you Miss Rarity." Mrs. Orange smiled.

"Oh you're quite welcome, I'm always willing to help a friend in need." Rarity smiled.

"Listen to my heart huh?" Applejack said almost to herself before sighing. "Okay, it wouldn't hurt to try that."

Applejack looked over towards Richie, thinking about all the details she liked about him. She also started to realize how handsome he really was, something she never thought of before. She was lost in her thoughts for a moment, until she realized that her heart was beating faster and her chest felt warm.

"Oh my...I don't believe it..." She almost whispered.

"Don't believe what?" Rarity asked.

Applejack suddenly felt a bit lightheaded, so she slapped her face and shook her head rapidly to snap herself out of it.

"I...I do love Richie." She admitted.

"I thought so." Mrs. Orange smiled. "You see dear, sometimes we just need to accept our feelings for another regardless of any complications we're afraid of."

"I certainly learned that." Rarity smiled. "You have to tell him Applejack, I can tell he loves you."

"Right..." Applejack hesitantly started walking towards Richie.

She could actually feel her heart starting to pound and she grew a little nervous, much to her surprise. After all Richie did love her back so there was nothing to be nervous about right? But then she realized: once she told him, there was no going back. And he lives in Manehattan while she lives in Ponyville, if they started dating they'd have to work around that detail along with her being busy on the farm and him being busy with his family's business. Could they really work everything out and remain happy together for the rest of their lives? But despite those fears, she knew that she still had to tell him. It wouldn't be fair to continue keeping her feelings a secret just because she wasn't sure of things, especially since he had already suffered so much.

Besides, she knew that at least her aunt wasn't going to leave her alone about the matter until she told Richie how she really feels.

"Um, Richie? I have to tell you somethin'." Applejack blushed as her heart continued pounding; she nervously 'toed' the ground with the tip of her hoof.

"What is-? Are you okay?" Richie asked concernedly.

"Yeah, just...just really nervous." Applejack admitted. "You see Rarity told me to listen to my heart about...well, about you. And I did and..." She gulped. "It turns out I...I love you."

"Wha-? You do?" Richie beamed. "Really? Because I love you too."

"I kinda figured...and yeah, I do. It's just...well we come from different cities - mine being more of a town - and we both have busy jobs so...how can we work things out? I've never balanced a very special somepony with a job before."

"Me either, especially since I haven't even started being a businesscolt." Richie chuckled. "Guess this'll just be a learning experience for us both. And you know, no matter what complications we may face I'm sure our love will help us through them."

"I...I hope so. I've never even been in love before." Applejack shrugged, looking away a bit.

"You know what? Neither have I." Richie smiled as he gently made Applejack look at him. "Maybe that's because we were meant to fall in love with each other from the very beginning. Who knows, maybe if you had stayed in Manehattan longer when we were foals we would've become friends and even something more long before today."

Applejack smiled.

"Maybe you're right...but what will we do after I move back to Ponyville?" She asked.

"We can always just keep in touch through letters and visit each other now and then." Richie pointed out. "But as for now let's just make the most of the time we have. Say, one of my favorite musicals is performing on Bridleway tonight if you'd like to go."

"Depends...which musical is it?"

"It's a comedy called The Sleepy Chaperone. It's about a famous actress who gives up life on Bridleway to marry her true love, only the producer she works for doesn't want to lose his leading lady and tries to sabotage it only for things to go crazy. The title character is the bride's chaperone, she has a condition that causes her to get sleepy from cider yet she can't stop drinking it."

"Well...since it's a comedy I wouldn't mind checking it out." Applejack smiled.

A.N. The Sleepy Chaperone is based on The Drowsy Chaperone, one of my favorite musicals.


	6. Getting the Orphans Settled In

Twilight, Pinkie, and Rainbow Dash then arrived with the orphans and Omar and Gloria Horsepitality, both of them unicorns.

"Richie!" Gloria and Omar called as they hurried over to Richie.

"Omar, Gloria!" Richie hurried over to them and they hugged. "I really missed you guys."

"We missed you too." Gloria said. "Thank you so much for giving us your house, you didn't have to."

"Of course I did, you and the orphans need a real place to stay and I have more room than I need."

"Hey Richie!" A little orange-tan pegasus colt with black hair came up to them.

"Hey Pee Wee, staying out of trouble?" Richie winked.

"Oh you know Pee Wee, trouble is attracted to him like a magnet." Omar teased.

"Ha ha, very funny." Pee Wee rolled his eyes.

The other orphans came up to Richie and greeted him as well.

"Hey, it's great to see you all too." Richie smiled to the orphans before addressing them individually.

Applejack smiled, loving Richie even more after seeing him interact with the orphans like a big brother. She could instantly see Richie being a great big brother for Apple Bloom, and also being a great little brother to Big Mac.

"Now, I know you already met a few of my new friends but there are two others I'd like you to meet." Richie then said. "This is Rarity, a fashionista who knows fashion like Gloria and Omar know orphan raising. And this beautiful mare is Applejack, my very special somepony."

Applejack blushed a little again. No one outside the family had ever called her beautiful before.

The orphans then greeted Rarity and Applejack, a lot of them stating how lucky Applejack was to have won Richie's heart.

"Richie is the best, he treats us like members of his own family." One colt said.

"We always knew that any mare who'd end up with him would be the luckiest mare in all of Equestria." A filly sighed, obviously a romantic.

"How did you two meet?" Another colt asked.

"Well, funny thing about that...I didn't exactly treat him nicely when we first met." Applejack said awkwardly. "My sibs and I had just spotted him sleepin' under one of our apple trees, and...well news of him being a thief had just reached Ponyville at the time..."

"Oh yes that was horrible what his uncle did to him." One of the older colts frowned. "We never believed it was Richie doing the stealing."

"We knew that the only thing Richie would ever steal would be a lucky mare's heart." Another obviously-romantic filly smiled.

"Yeah." Applejack blushed. "Well my little sis had become good at readin' Cutie Marks and noticed that Richie's didn't relate to stealin', so we let him tell us his side of the story. I'm good at readin' honesty, so I could tell that he was tellin' the truth and offered to help him get his home and reputation back."

"And she and her friends did." Richie smiled. "Now, the rooms are nearly complete and we have beds for you all, so it's best that we get all of you settled in. For one thing you'll need to pick what designs you want on your bedroom walls, then we'll have to get those designs painted on. Omar, Gloria, the nursery is complete if you want to move the babies in now."

"That would be for the best, that way we'll be free to help the other foals move in." Omar nodded.

"However one of us will have to keep an eye on the babies." Gloria pointed out.

"Can I babysit?" Pinkie grinned. "I've had loads of practice with the Cakes' twins."

"The Cakes?" Pee Wee said.

"My employers, they run a bakery in Ponyville." Pinkie explained. "I live with them above it."

"Oh."

"In that case of course you can Pinkie." Gloria smiled. 'Thank you."

"No problemo." Pinkie grinned.

After getting the babies settled into the nursery and leaving Pinkie to babysit the others got work on the rest of the bedrooms. Fortunately the foals had already decided on generic designs for the walls, to be fair to future orphans, so it didn't take long to finish the painting. Twilight and Rarity then decided to go shopping for sheets and other necessities, so Omar went with them to help them select the right colors and patterns.

After the paint had dried the beds were moved into the bedrooms, and once Twilight, Rarity, and Omar came back with the necessities the beds were made, toiletries went into the bathrooms, etc.

As for Richie's parents' old bedroom, Omar and Gloria decided that it was a little too fancy for their tastes so the furniture was moved up into the attic. They would work on getting some new furniture later, after the foals were done settling in.

"Need two beds so that you can throw totally awesome sleepovers?" Pinkie grinned to Richie, bouncing at the idea.

"Not really, I just need some time to decide which bed I prefer for my own." Richie explained before looking a little sad. "I'm...kinda finding it hard to get rid of any of my parents' things."

"No sweat, you've got loads of time to decide." Rainbow Dash smirked.

"Very true." Richie now smiled.

During all this Twilight, Rainbow Dash, and Pinkie found out about Richie and Applejack having become official very special someponies. They were all very happy for them.

"I am totally throwing you two a 'Congratulations on Being Very Special Someponies' party!" Pinkie bounced.

"Oh that...that isn't necessary cuz." Applejack blushed, this time out of embarrassment.

"Yeah..." Richie also blushed out of embarrassment.

"Pinkie dear, they have barely started dating. I think it'd be best if you wait until they've gotten used to this." Rarity said. "Dating after all is a major step in anypony's life."

"Aw..." Pinkie pouted.

"It's okay Pinkie, I am planning on throwing a celebration in one of the hotel ballrooms later. You can help me plan that instead." Richie smiled.

"Okay!" Pinkie beamed.

"Celebrating the new orphanage being completed right?" Twilight smiled.

"Yeah, plus I thought it'd be a good way for me to meet your family and the rest of your friends." Richie smiled. "So you're all welcome to invite whoever you want."

"Hey awesome!" Rainbow Dash grinned.

"Can I invite Princess Celestia and Luna as well?" Twilight asked.

"Of course, if they can make it. I don't want them to cancel anything important just for this." Richie said.

"Oh don't worry, Princess Celestia loves hearing about generous moments like this and Luna has a fondness for foals. I'm sure they can make a little room in their schedule."

"Okay...wait, you don't address Princess Luna by her title?"

"She insisted on it a long time ago." Applejack smiled. "She prefers to think of herself as our friend rather than our ruler."

"Oh."


	7. Earning a Happy Ending

Later that evening Twilight, Rainbow Dash, Rarity, and Pinkie Pie headed for the hotel - an inexpensive one since they had no idea how long they'd be staying in Manehattan - while Applejack and Richie went out on their first official date. Applejack stopped by the hotel to get cleaned up first though, wanting to look at least decent since this was her first date ever. Rarity also insisted that she dress up for the occasion, but Applejack refused. They finally compromised by Rarity letting Applejack borrow one of her simpler ruby necklaces.

"That is a beautiful necklace." Richie smiled.

"Thanks, but it's actually Rarity's. She insisted that I look nice for our date." Applejack shrugged.

"Well even so it does look beautiful on you. But don't worry, I prefer your natural look to a dressed-up look." Richie said before opening the door to his family's carriage (Herbert was pulling it).

"Glad to hear that...an open-top carriage?" Applejack looked the carriage over, used to closed-top carriages in Manehattan.

"Oh it has a top, my parents and I just always preferred it down during clear days." Richie said. "We like watching the view."

"Heh, gotta admit I prefer watchin' it to participatin' in it." Applejack chuckled.

"Yeah, it can get crazy around here at times." Richie chuckled back. "But I got used to it. Even so I do prefer calm days to crazy ones, not that much of a city pony. Yeah there are plenty of things to do in a city, but there aren't that many places to play."

"I hear ya." Applejack agreed.

They continued talking a bit until they reached the theater where The Sleepy Chaperone was playing.

"I'll meet you two back here after the play, going to do a bit of shopping." Herbert said. "I want to make sure there'll be plenty of food for Gloria, Omar, and the orphans for a while."

"All right, see you later Herbert." Richie smiled.

"Bye Herbert." Applejack waved as Herbert trotted off.

They then went inside and Applejack enjoyed the play from the beginning. The set-up was really cool, it first opened in a stallion's apartment. The stallion greeted the audience and explained that he was feeling blue and so decided to play one of his records, which happened to be The Sleepy Chaperone. Then as the musical part started the stallion's apartment altered itself to resemble the lobby of a mansion. Said mansion belonged to an absent-minded mare who was hosting the wedding. The other characters entered singing their own introductions, including two gangsters who were posing as bakery chefs. There was even a pegasus who flew other ponies from one place to another for a living.

Sure enough Richie was right, the musical was definitely a comedy. Applejack laughed along with Richie for at least half of the play, enjoyed the music, and loved how the groom obviously loved his bride for herself instead of for being a famous and attractive actress.

After the musical they went straight to dinner, this time a restaurant that was slightly fancier than the last one they went to yet still served good portions.

"I'll be right back, I have to use the little colt's room." Richie said before leaving.

"No prob." Applejack smiled as she slid into the booth they were going to eat at.

However they weren't alone, a pony Applejack didn't expect to see soon entered the restaurant. Trenderhoof. He instantly spotted Applejack and went over to her.

"Applejack? Fancy meeting you here." Trenderhoof smiled.

On the outside Applejack tried not to look annoyed, but on the inside she groaned. Before tonight she hoped she would never have to deal with his flirting ever again.

"Yeah, fancy that." She deadpanned.

"It must be fate, us meeting in the same restaurant in Manehattan of all places. Listen I still really like you and would like to get to know you more. May I join you?" Trenderhoof lifted Applejack's hoof as if he was going to kiss it.

"Mr. Trenderhoof? Well hi there, I recognize you from your articles." Richie smiled, having just returned.

Applejack said a prayer of relief in her mind.

"Well Mr. Richie Fillyanthropy. I'm glad you showed up, I came here looking for an interview." Trenderhoof smiled. "I heard about your generous act of turning your home into the new orphanage and want to do an article on it."

"Sure thing, but it'll have to wait until tomorrow. I'm on a date right now." Richie said before getting into the seat opposite Applejack's.

Trenderhoof's smile turned into a look of shock.

"Oh...you two are dating?" He said.

"Yeah, we met in Ponyville when my uncle had me banished from Manehattan and she and her friends helped me clear my name." Richie smiled. "I fell in love with her about three days ago and she returned my feelings today."

"Eeyup." Applejack smiled at Richie lovingly, partly because she really did love him and partly because she hoped it would help get Trenderhoof to finally leave her alone.

Richie blushed at the way she was looking at him, and couldn't help but smile lovingly back at her.

"I see...I'll leave you two alone now...I'm kinda hungry anyway." Trenderhoof said awkwardly and disappointedly before going to find an empty table.

"Hope we didn't embarrass him." Richie said sympathetically. "It can't be easy losing the mare you like."

"I'm sure he'll get over it, he only had a crush on me. Besides, no one was really looking at us." Applejack pointed out.

"True."

They then ordered dinner and switched the conversation to more pleasant topics. After dinner they left to walk back to the hotel, since the restaurant was close enough to it for that.

"Um, hello again." Trenderhoof caught up to them awkwardly. "Sorry to intrude on your date like this, but I can't help wondering: Mr. Fillyanthropy, how did you win Applejack over?"

"Look, Trenderhoof, originally I just wasn't into datin' in general because I'm a workin' mare and put my family first." Applejack said. "But after I met Richie, well, I couldn't help but fall in love with him. You see, yer simply not my type and he is. I need somepony who has a strong love of family, who's willin' to work hard at what they do for a livin', and who's willing to help others no matter the cost. Plus, to be frank, somepony humble. And that's Richie."

"Ah...I get it." Trenderhoof was still disappointed, but he wasn't going to be a sore loser. "I accept my loss. Congratulations Mr. Fillyanthropy, you won the heart of the finest mare in all of Equestria."

"I know. And don't worry Mr. Trenderhoof, if you just stick to being yourself and not worry to much about impressing others then you'll find your very special somepony someday." Richie smiled.

"I...thank you for being understanding and compassionate about this." Trenderhoof smiled, touched by Richie not acting like a possessive jealous boyfriend. "Please, call me Trend."

"Only if you call me Richie." Richie chuckled, extending his hoof.

"Deal." Trenderhoof shook it. "I'm looking forward to tomorrow's interview."

"So am I." Richie smiled.

They said their goodbyes and went their separate ways. Richie and Applejack continued on into the hotel and up to the room where she and her friends were staying.

"Well...goodnight." Applejack said awkwardly.

"Goodnight." Richie said awkwardly.

They hesitated. Should they kiss now, or should they wait until later? Deep down Richie did want to kiss her, but he didn't know whether she was ready or not. And Applejack did feel a desire to kiss him, but she didn't know whether it was too early or not.

"OH JUST KISS ALREADY!" Pinkie's voice screamed through the door.

"Pinkie!" Twilight's voice said irritatedly.

Richie and Applejack then heard the sound of bodies falling onto the floor. Caught off-guard, Applejack opened the door to see Twilight and Rainbow Dash pinning Pinkie to the floor and muzzling her with their hooves. Twilight and Rainbow Dash grinned embarrassedly upon seeing Applejack and Richie stare at them. Rarity just facepalmed at the whole thing.

"Heh, maybe we should save our first kiss for later." Richie smirked.

"Yeah, especially since there's somepony I need to take care of right now." Applejack smirked back.

Twilight and Rainbow Dash got out of the way just as Applejack tackled Pinkie.

"Okay cuz, if yer gonna invade other ponies' privacies then yer gonna have to suffer the consequences." Applejack grinned before noogying Pinkie.

Richie, Rainbow Dash, and Twilight laughed and Rarity politely chuckled at the scene.

"Okay okay! Uncle! Uncle!" Pinkie cried.

Applejack let her go, and the two of them laughed.

"Applejack, would you like to go out to dinner again tomorrow night?" Richie asked.

"Sure, but how about we make it a picnic in the park instead of a meal in a restaurant?" Applejack suggested.

"Sounds great to me. Well, goodnight everypony." Richie smiled before leaving.

Applejack and her friends said their goodnights too.

"So, how'd it go?" Rainbow Dash asked.

"It went great gals. I can see myself dating Richie for a long time." Applejack smiled. "However I want Granny Smith, Big Mac, and Apple Bloom to get to know Richie some more before making it official. So I'm thinking of inviting Richie to Sweet Apple Acres after the celebration."

"That's a good idea, there's no sense in ending up with somepony your family doesn't like." Twilight agreed.

"Although I'm certain your family will love Richie." Rarity smiled.

"Yeah, who wouldn't love a guy like Richie? Well maybe a meanie-pants, but that's not surprising." Pinkie grinned.

"True." Applejack chuckled.

That afternoon Trenderhoof interviewed Richie, and the two became good friends during it. When Richie brought up the secret passageways in his home Trenderhoof expressed concern towards the orphans finding out, but Richie reassured him that he used a spell to seal up the secret entrances back before the painters had even started working on the bedrooms. Nopony can get into the secret passageways without Richie casting another spell to open the entrances now.

Later that night Richie and Applejack had their picnic in the park. And after dessert, they finally had their first kiss. The love they felt from it was so strong that for a long time Applejack stopped being afraid of how they were going to balance their jobs and dating. And as for Richie, the emptiness he had felt ever since his parents died was finally filled.


End file.
